I’m Glenn Gow, The Scaling Executive Coach and host of The Scaling Executive Podcast. I talked with Mike Winterfield, founder and managing partner of Active Impact Investments, Canada’s largest climate tech seed fund, about the mistake he sees seed-stage founders make most often: giving away sales too soon.
When a seed-stage founder hands sales off to a new hire before reaching product-market fit, Mike Winterfield holds that the company loses the one person who can stay close enough to customers to diagnose the real problem, the pricing, and the ROI, a mistake Winterfield has watched repeatedly across the 45 startups Active Impact Investments has backed over more than eight years.
Winterfield has scaled Active Impact Investments over nine years into a certified BCorp with $180 million in assets under management across three limited partnership funds. Before venture capital, he was President of Traction Rec and COO of Traction on Demand, which grew into Canada’s largest dedicated Salesforce implementation partner, and earlier in his career managed a $300 million revenue portfolio as President of Randstad Professionals.
This episode is for seed and early-stage founders deciding when, and how, to hand off the sales process they’ve been running themselves.
Key Takeaways
- Seed-stage founders most often try to give up founder-led sales too early, often by hiring a salesperson before reaching product-market fit, which Mike Winterfield calls “a ridiculously hard sales hire to make” because no outside hire can yet diagnose the problem, ROI, and pricing the way a founder embedded with customers can.
- When founder-led sales does need to scale, the fix isn’t a full handoff. Winterfield recommends hiring someone to absorb the lowest-value parts of the sales process, prospecting, outreach, demos, while the founder stays personally involved at the sales process’s “moment of truth,” with both owning deals together rather than working separately.
- New sales leaders who try to force their personal selling system onto a team often fail. Winterfield says he became a more effective sales manager only after he stopped teaching his own method and started observing and celebrating each rep’s individual selling style.
- Investors and advisors get more traction with founders by giving probabilistic, evidence-based context, citing what has and hasn’t worked across a portfolio, rather than issuing definitive directives, and by asking diagnostic questions before offering advice so founders self-identify their own gaps.
- Active Impact Investments evaluates AI opportunities in climate tech through two lenses: whether the product itself is AI-native and differentiated for customers, and whether the company is using AI operationally to run leaner and more efficiently across departments.
How Founders Should Decide When to Delegate Sales
Winterfield is direct about the pattern he sees across his portfolio: “I see founders trying to give that away, a little too quickly.” Technical founders and co-founders without a sales background, he says, often feel intimidated and assume the fix is simple: hire a salesperson and the problem goes away.
That instinct backfires before product-market fit. “That is a ridiculously hard sales hire to make is when you won’t have product market fit yet,” Winterfield said, because the role requires someone willing to “stumble around in the dark” to figure out the customer’s real problem, the right pricing, and the ROI case, work he believes only the founder is positioned to do well in the early days. His advice for that stage: “Fall in love with the problem. Don’t fall in love with your solution.”
The transition away from founder-led sales isn’t a single handoff. Winterfield describes a sequence:
- Keep selling personally until the workload, not your discomfort with sales, becomes the constraint
- Hire someone to take over the lowest-value parts of the process first: building a prospect list, initial outreach, running demos
- Stay personally involved at the moment in the sales process where it’s most effective to have the CEO in front of the customer
- Review key documents like a statement of work before it goes out, even if you didn’t build it: roughly five to ten minutes of review against three hours of drafting
The goal, in Winterfield’s words, is to “work together to double my capacity or triple my capacity,” with the founder and the new hire owning deals jointly rather than splitting the pipeline and working separately.
How New Sales Leaders Build a Team Instead of Cloning Themselves
Winterfield’s own leadership lesson came from climbing the ranks at Randstad Professionals, where he eventually managed a $300 million revenue portfolio as President, after starting as an individual contributor and becoming one of the top salespeople in the country.
His first attempt at leading a sales team failed. Early in his career, he tried to teach every rep the exact system that had worked for him, tracking the same funnel numbers and conversion benchmarks he had been taught. “I would say that I failed at doing that in the early days,” he said.
The shift came from watching his team instead of teaching them. Winterfield noticed reps succeeding with completely different approaches: “There was a big bag of tricks out there and many different ways to skin a cat.” Once he started observing and celebrating those differences rather than standardizing them, he became both more effective and more likable as a manager, with a larger toolkit of approaches to share with each rep based on what actually worked for them individually.
How Investors Should Advise Founders Without Dictating to Them
Moving from operator to investor changed how Winterfield exercises influence. Employees report to a leader and have to follow direction; founders do not report to an investor and are free to ignore advice entirely. Winterfield’s response was to adopt what he calls a servant leadership approach, framing guidance as probability rather than command: “90 percent of our founders who’ve tried it, it hasn’t worked for them,” rather than telling a founder flatly that they are wrong.
He also names a mistake he made early as an investor: prescribing before diagnosing, offering sales-ops coaching before he actually knew where a founder was strong or weak. His fix was to lead with questions, asking founders to walk through their own sales pipeline and explain how they manage it, before offering any advice at all. Founders who can answer those questions confidently often don’t need the coaching. Founders who can’t tend to realize it themselves, which Winterfield says makes them far more receptive to help than being told they need it.
That same philosophy extends to how he views the investor-founder relationship structurally. Winterfield believes investors and founders should sit on the same side of the table rather than operate from a perceived hierarchy, a dynamic he says shows up most often on boards with members who have never run operations or managed teams themselves.
How CEOs Should Evaluate AI as a Product Feature or an Operational Tool
Across Active Impact Investments’ portfolio, Winterfield says the first wave of AI productivity gains concentrated in two places: content production, where tasks that used to take hours started taking minutes, and software engineering, where teams could run leaner. CEOs who acted on those gains roughly a year ago by adjusting headcount in marketing, communications, and engineering fared better over the following year than CEOs who didn’t. “The range of things that people are using AI for, is absolutely exploding,” he said, pointing to customer service and sales as newer areas of expansion.
When deciding where to invest, Winterfield applies two separate lenses. The business use case asks whether AI is a differentiated part of what the company actually sells, a vertically specialized solution built around an easier interface, proprietary data, or agentic capability. The operational use case asks a different question entirely: is the company running its own internal functions more efficiently because it uses AI as a tool across departments, independent of what it sells to customers.
How to Scale a Company: The Framework
| Principle | What it means | Named evidence from this interview |
| Keep sales founder-led until it breaks, then delegate the easy parts first | Don’t hand off the entire sales function to a new hire before product-market fit; delegate prospecting, outreach, and demos while staying personally involved at the moment of truth | Across 45 startups backed by Active Impact Investments over eight-plus years, Winterfield has repeatedly seen founders give away sales too early, calling an early sales hire “a ridiculously hard sales hire to make” before product-market fit |
| Don’t clone yourself, build a toolkit from your team’s differences | A new sales leader gets more out of a team by observing and celebrating each rep’s individual selling style rather than forcing everyone to follow the leader’s own system | Managing a $300 million revenue portfolio at Randstad Professionals, Winterfield initially tried to make every rep replicate his own top-performing sales method and failed, succeeding only after he started sharing what worked for each individual rep |
| Diagnose before you prescribe, and speak in probabilities | Ask diagnostic questions before giving advice so founders self-identify their own gaps, and frame guidance as evidence from a portfolio rather than as a directive | Winterfield now opens with questions like asking a founder to walk through their sales pipeline rather than coaching blind, and frames advice using outcomes like “90 percent of our founders who’ve tried it, it hasn’t worked for them” instead of telling founders they are wrong |
| Evaluate AI through two lenses: the product and the operation | Separate whether AI is a differentiated part of what a company sells from whether AI is making its internal operations leaner | Active Impact Investments saw early AI gains concentrate in content production and engineering, and says portfolio CEOs who cut bloated marketing and engineering headcount roughly a year ago fared better over the following year |
Quotes from This Episode
- “I see founders trying to give that away, a little too quickly.” (Mike Winterfield, Founder and Managing Partner, Active Impact Investments)
- “There was a big bag of tricks out there and many different ways to skin a cat.” (Mike Winterfield, Founder and Managing Partner, Active Impact Investments)
- “90 percent of our founders who’ve tried it, it hasn’t worked for them.” (Mike Winterfield, Founder and Managing Partner, Active Impact Investments)
- “How can we work together to double my capacity or triple my capacity?” (Mike Winterfield, Founder and Managing Partner, Active Impact Investments)
- “The range of things that people are using AI for, is absolutely exploding.” (Mike Winterfield, Founder and Managing Partner, Active Impact Investments)
Frequently Asked Questions
When should a founder hire a salesperson?
Mike Winterfield, founder and managing partner of Active Impact Investments, says founders should keep selling personally for as long as possible and avoid hiring a salesperson before reaching product-market fit. Winterfield calls an early sales hire “a ridiculously hard sales hire to make” because the role requires someone who can diagnose the customer’s problem, pricing, and ROI from scratch, work he believes the founder is best positioned to do while staying close to early customers.
How should an investor or board member give advice to a founder?
Mike Winterfield, founder and managing partner of Active Impact Investments, starts by asking founders diagnostic questions, such as asking them to walk through their sales pipeline, instead of offering advice before understanding where they are strong or weak. Winterfield says founders become more receptive to help when they identify their own gaps themselves, and prefers framing guidance in probabilities drawn from his portfolio, such as noting that 90 percent of founders who tried a particular approach found it didn’t work, rather than telling a founder they are doing something wrong.
How should investors evaluate AI when deciding where to invest?
Mike Winterfield, founder and managing partner of Active Impact Investments, evaluates AI opportunities in climate tech through two separate lenses. The first is whether the product itself is AI-native or vertically specialized in a way that’s differentiated for the customer. The second is the operational use case, whether the company is running its internal functions more efficiently because of AI. Winterfield says portfolio companies that made AI-driven efficiency adjustments to marketing and engineering headcount roughly a year ago fared better than those that didn’t.
CEOs Work with Glenn Gow to Scale Their Companies and Themselves
Glenn Gow is The Scaling Executive Coach. He coaches ambitious executives into the CEO seat and CEOs into successful exits, drawing on 25 years as a CEO and five years in venture capital. If this conversation was useful, you can apply for executive coaching with Glenn Gow or apply to be a guest on The Scaling Executive Podcast.
